Réaction #324423

ord-10a7f6fc613245f38e6fe1fe9362ea29

Équation de réaction

C[C@@H](C(=O)O)N(C)C(=O)OC(C)(C)C
Boc-N-Me-Ala-OH
COC(=O)[C@@H]1C[C@H](N=[N+]=[N-])CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C
title compound
COC(=O)[C@@H]1C[C@H](N=[N+]=[N-])CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C
(2S,4S)-methyl 4-azido-1-((S)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoyl)pyrrolidine-2-carboxylate
O=C(O)C(F)(F)F
trifluoroacetic acid
O=C(O)C(F)(F)F
trifluoroacetic acid
→
COC(=O)[C@@H]1C[C@H](N=[N+]=[N-])CN1C(=O)[C@@H](NC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C)C(C)(C)C
title compound
COC(=O)[C@@H]1C[C@H](N=[N+]=[N-])CN1C(=O)[C@@H](NC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C)C(C)(C)C
(2S,4S)-methyl 4-azido-1-((S)-2-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-3,3-dimethylbutanoyl)pyrrolidine-2-carboxylate

Réactifs

C[C@@H](C(=O)O)N(C)C(=O)OC(C)(C)C
Boc-N-Me-Ala-OH
COC(=O)[C@@H]1C[C@H](N=[N+]=[N-])CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C
title compound
COC(=O)[C@@H]1C[C@H](N=[N+]=[N-])CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C
(2S,4S)-methyl 4-azido-1-((S)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoyl)pyrrolidine-2-carboxylate
O=C(O)C(F)(F)F
trifluoroacetic acid
O=C(O)C(F)(F)F
trifluoroacetic acid

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

The title compound of Example 1 was treated with trifluoroacetic acid using the general procedure A to deprotect the BOC group. The resulting trifluoroacetic acid salt was coupled to Boc-N-Me-Ala-OH using the general procedure D to prepare the title compound of Example 2. 1H NMR (CDCl3): consistent with proposed structure.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08642554B2uspto-grants-2014_02